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Catalytic Asymmetric Direct Vinylogous Aldol Reaction of Isatins with β,γ-Unsaturated Butenolides.
Chemistry. 2017 Nov 21; 23(65):16447-16451.C

Abstract

A direct asymmetric vinylogous aldol reaction of nonactivated natural α-angelica lactone to isatins has been developed. With a N,N'-dioxide-Sc(OTf)3 complex as catalyst, a variety of δ-hydroxy butenolides bearing congested adjacent tetrasubstituted stereocenters were obtained in good yields with high diastereoselectivities and excellent enantioselectivities. Besides, a possible transition state was proposed to explain the origin of the asymmetric induction.

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Authors+Show Affiliations

Tang Q
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
Lin L
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
Ji J
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
Hu H
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
Liu X
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
Feng X
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28960577

Citation

Tang, Qiong, et al. "Catalytic Asymmetric Direct Vinylogous Aldol Reaction of Isatins With β,γ-Unsaturated Butenolides." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 23, no. 65, 2017, pp. 16447-16451.
Tang Q, Lin L, Ji J, et al. Catalytic Asymmetric Direct Vinylogous Aldol Reaction of Isatins with β,γ-Unsaturated Butenolides. Chemistry. 2017;23(65):16447-16451.
Tang, Q., Lin, L., Ji, J., Hu, H., Liu, X., & Feng, X. (2017). Catalytic Asymmetric Direct Vinylogous Aldol Reaction of Isatins with β,γ-Unsaturated Butenolides. Chemistry (Weinheim an Der Bergstrasse, Germany), 23(65), 16447-16451. https://doi.org/10.1002/chem.201704100
Tang Q, et al. Catalytic Asymmetric Direct Vinylogous Aldol Reaction of Isatins With β,γ-Unsaturated Butenolides. Chemistry. 2017 Nov 21;23(65):16447-16451. PubMed PMID: 28960577.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic Asymmetric Direct Vinylogous Aldol Reaction of Isatins with β,γ-Unsaturated Butenolides. AU - Tang,Qiong, AU - Lin,Lili, AU - Ji,Jie, AU - Hu,Haipeng, AU - Liu,Xiaohua, AU - Feng,Xiaoming, Y1 - 2017/10/26/ PY - 2017/08/31/received PY - 2017/09/24/revised PY - 2017/9/30/pubmed PY - 2017/9/30/medline PY - 2017/9/30/entrez KW - N,N′-dioxides KW - aldol reactions KW - isatins KW - lactones KW - scandium SP - 16447 EP - 16451 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 23 IS - 65 N2 - A direct asymmetric vinylogous aldol reaction of nonactivated natural α-angelica lactone to isatins has been developed. With a N,N'-dioxide-Sc(OTf)3 complex as catalyst, a variety of δ-hydroxy butenolides bearing congested adjacent tetrasubstituted stereocenters were obtained in good yields with high diastereoselectivities and excellent enantioselectivities. Besides, a possible transition state was proposed to explain the origin of the asymmetric induction. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/28960577/Catalytic_Asymmetric_Direct_Vinylogous_Aldol_Reaction_of_Isatins_with_βγ_Unsaturated_Butenolides_ DB - PRIME DP - Unbound Medicine ER -